Millennial Money Man

Helping Millennials Make More Money, Save More, and Pay Off Debt

June 12, 2017

7 Lessons I’ve Learned In Two Years of Self-Employment

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7 Lessons I’ve Learned In Two Years of Self-Employment

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Two years ago this month, I walked into my principal's office at the high school I had taught at for three years to do my exit interview. It's basically the last step in the resigning process, so I had already gotten through about a month of the awkward stuff that happens long before the interview.

Even though literally nobody understood why I was leaving or thought it was a solid plan, there weren't any hard feelings (that I know of). I didn't quit my job for any other reason than I was really passionate about personal finance and had a dream of owning my own business.

When I decided that I wanted to quit my band director job to run M$M full-time, I simultaneously made the decision that I was going to be as helpful as I possibly could until my last day at the school.

That included giving my thoughts on who should replace me, and even actively trying to recruit people that I thought would be best for the job.

Then, there was telling the kids that I wouldn't be there anymore (which was by far the most difficult part – kids tend to take teachers moving on to different things really hard sometimes). That was one of the few times in my life that I got legitimately choked up while I was talking to a group.

By the time I got to the exit interview, it was a piece of cake. The principal basically said, “Congrats, you're chasing your dreams and that's really cool,” and that was it. I drove away from the band hall a few days later for the last time and completely changed careers.

Now two years later, I've been able to really reflect on what it took to get to this point (and appreciate that I actually made it this far haha).

Here are 7 things I've learned about self-employment and blogging full-time in my first two years:

1. There is no exact blueprint for business success

Most people describe leaving your job for self-employment as a leap of faith, but now I really look at it differently. There is no blind leap that magically ends by landing on success.

It's way more like purposely falling into the deep end of a pool and not knowing how to swim at all.

Even two years later, I'm still trying to figure out what works and what doesn't, how to sell, what to charge, etc.

There are definitely guidelines you can follow, but everyone's path in business is different. Your strengths really determine what you'll focus on (especially in a solopreneur model like my business).

2. Business is pretty cut and dry

When I was a teacher, things seemed really complicated most of the time. I was asked to do things because “that was just how it was done” (like going to meetings that had literally nothing to do with me).

If you pushed back on things like that, you got your wrist slapped by an administrator.

Business is inherently different, especially from the ownership side of things. It's about making money. In my case it's also about helping people feel better about money and entertaining people as well, but if I'm not making money I can't do those things.

That might seem soul-less to a lot of people, but for me, it seems really simple and cuts a lot of drama and wasted time out of the equation. If you are doing something and it's profitable and good for your customer, keep doing it. If it's not profitable, do something else until it's profitable.

I don't have to do things “just because”. I do things that I think will grow the business and my brand.

3. The money is never enough and won't make you happy

I could have sworn that when I was making $50,000 a year that $100,000 would make me happy. It's not like I was unhappy though; I just thought that more money would make me even happier.

Ha surprise! Doesn't work that way at all (I can feel the collective eye roll and the, “Yeah, I'd like to see for myself“….but I know I'm right on this and do hope you find out someday).

Once I was making $100,000, I wanted $150,000. It looks like I'll probably make around $200,000 this year, and now my goal is $500,000 next year. Once I hit $500,000, I'll want $1,000,000.

Then I'll want $2,000,000, and then $5,000,000 and so on and so on.

If you aren't a fan of the pursuit, you can go nuts chasing a moving target like that because you won't be fulfilled when you hit the next big number. Fortunately, I enjoy the game a lot and understand now that the money isn't what drives happiness.

Read also: Does a higher salary lead to happiness?

4. You have to admit what you suck at and embrace what you're great at

Confession: I suck at sales meetings and pitching services to clients. I went on several face to face sales meetings when I first started running my business full-time, and they never worked haha.

I'd dress nicely and practice my talking points, but it just never went the way I wanted it to. I was always so uncomfortable, and I'm sure that showed when I was talking to a potential marketing client.

Now I just don't really do them anymore. Most of the marketing work I've secured was fully via emails, which is where I communicate the most effectively (I do write for a living after all).

That doesn't mean I won't do one if I have to, but I'm going in as myself and will let my previous and current work do the talking for me.

I will say though – I'm a lot more confident now than I used to be because I've had some success. I can sit down with a client and basically say: “I built one of the biggest millennial personal finance blogs in the world in less than two years using Facebook ads.”  Boom.

Also, I don't technically need new clients because I have so many income streams. It makes it easier to negotiate because they need me, not the other way around.

5. Growth is slow but seems to happen fast

This sounds a little oximoron-ish, but anyone that has owned a business would probably agree. When you're in the grind trying to make more sales or get more clients – it seems like it takes forever.

Then you sit down and look at where your business is compared to a year or two years ago, and it feels like it happened so fast!

6. Relationships are key

The saying ,”It's not what you know, it's who you know,” is 100% true.

Most of the gigs that I've gotten on the marketing side of my business so far didn't come from making random phone calls or spamming business owners' inboxes.

They came from getting a strong referral from friends or people that I had done good work for. That's why you have to make sure that you always do your best work (the same goes for blogging – my readers tell other people about my site because they like the content).

The other part of the referral equation is to always do business with integrity and treat people right. I could overcharge someone for setting up their Facebook marketing, but I'll make four times as much money when I treat the client right and get referrals to their business-owning friends.

7. Nothing is free. Ever.

As a teacher, I did a lot of free work. It was expected that you volunteer to do certain tasks or stay later without extra compensation. It always bothered me, but that's just the way it was and it works for that industry.

In business, people don't do free stuff. Even if there isn't financial compensation for something, it better provide value that I can use to make more money later on.

I'll do something for free if you can hook me up with a journalist that will write a story about my site. See what I mean?

There's nothing wrong with being nice to other people and helping them out, but there should always be a value proposition involved.

Where is M$M going to go in the future?

Honestly, I'm not totally sure yet. I'm going to start working on my marketing course for bloggers this summer, and will also take some time off to recharge the batteries so I can keep grinding again. If you want to get in on the course, sign up for the waiting list below.

The marketing course will cover:

  • How to use your existing blog or one you're going to start soon to get marketing clients
  • Every aspect of setting up a profitable, sustainable marketing business from your laptop
  • What to charge for your services
  • How to build your blog alongside your marketing business
  • Legal structures you should use and how to pay yourself as a business owner
  • Facebook marketing, SEO, Google Adwords, email campaigns, web design, and more!

Drop your email in the area below and you'll get updates on the course and exclusive marketing tips and content from me:

FB Ads for Bloggers Waitlist

Learn how to grow your blog and audience quickly with inexpensive FB ads. (Launches late August 2018)

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Here's to another two years! 🙂

Live differently. Your bank accounts will thank me later. ~M$M

Don't miss another M$M post.

Learn more about attacking debt, making more money, and creating an awesome life you love.

Comments

  1. Great stuff, I especially agree that integrity is key. And I love the purposefully falling into a pool line. I heard someone say that it’s better to be a really good opportunist than an ok planner. Take opportunities as they come up and crush them, and you’ll look up a few steps down the road really successful!

    To answer your question, I like the idea of being good enough at self-employment to have steady pay haha.

    Reply

  2. Congrats on two years (and more to come!) I remember way back when I came across your blog (and had no yet subscribed, ha)! Time flies. You’ve certainly grown and proven that running a business from scratch, is possible!

    I would love to run my own business one day…just not sure if I want it to be my blog or flipping homes 😉

    Reply

    • I’d highly suggest it if self-employment is what you want! I felt trapped in a normal job, but that’s just me. Yeah it’s crazy, can’t believe how far everything has come in just two years.

      Reply

  3. Good stuff, Bobby!

    Congrats on making it 2 years and thank you for everything you’ve written about. I greatly enjoy reading your posts and would be lying if I didn’t admit that much of my personal successes weren’t partially due to reading countless posts on M$M.

    As I work towards developing my own content, it’s funny how rewarding it seems to put good ideas into an article. With that being said it does seem like things move SO SLOW, but in the end it’s a wild and fun ride nonetheless.

    Again, congrats on all your success!

    Reply

  4. I love hearing your story, and how you took the leap of faith. Where I’m struggling, is my career is pretty lucrative and I would be hard pressed to start something that would make me equal or more money. I’m trying to get to a point where what I make just doesn’t matter, and I can take the leap of faith having removed the fear / need to make a certain $ amount… it’s a challenge to figure out the balance. How to begin the journey part time, without pulling too much time away from my career that gives me more $ when I dedicate more time to it. Love watching your journey continue to unfold, and learn a lot from your success and advice.

    Reply

    • I’m glad it helps Michelle! I really enjoy writing about it – it’s always fun to go back and re-live it a bit. Easily the scariest thing I’ve ever done haha.

      Yeah the balance is tough. You’ll NEVER see the “perfect” time to pursue something else and I guarantee you’ll still be scared when you do it haha. Just part of it.

      Reply

  5. Congrats on two successful years! Your story has been inspirational and the insight you share is always very helpful. I’m glad to hear there’s not nearly as much ‘office politics’ when you’re your own boss. Looking forward to continued progress!

    Reply

  6. Appreciate the honesty! I am on the precipice of jumping into self-employment and I’m really excited and a bit terrified. But I believe in myself and the value I can bring so here goes nothing!

    I completely identify with feeling trapped in full time employment. I look forward to never again having to ask permission to travel! Since I’ve realised that’s such a big priority for me, I’m making sure that my next move is fully location-independent.

    Congrats on 2 years and thanks for the inspiration and motivation!

    Reply

  7. Love when you write about being an entrepreneur. When my wife and I came across your site over a year ago we were blown away by the useful content and your story of leaving your job.

    It was a huge motivating factor for us to grind on our site for 9 months while were both working full time (and going to school). We would get home and blog. Weekends consisted of blogging. We would turn down friends so we could work on our blog. That “grind” set us up so I could feel comfortable leaving my job.

    Since quitting my full-time job I have never been happiness. The FREEDOM that comes with working for yourself is unreal. Something that I always wanted but never realized how incredible is really is.

    I have not replaced my income by any means yet but by the end of the summer, we should be close to replacing it.

    Exciting to see other bloggers in the personal finance niche continue to grow and see success.

    Can’t wait to take your course. I recently landed a freelance job on Upwork in digital marketing. Perfect for learning more about digital marketing and getting paid.

    As alway thanks for being so honest.

    Reply

    • There is a lot of freedom for sure! It took me a while to fully replace my income, and I only was able to do it through marketing. I really think this course is going to help people make some good money!

      Reply

  8. #3…I think that this is the single most important point for new bloggers to understand. I have made money from my sites in the past. I always think that when I cross that next threshold that I’m going to be satisfied with the earnings and feel like I’ve ‘made it’. Really, it’s always an uphill climb and your goals need to be much bigger than money or you’re more likely to fail.

    Another great article, thanks!

    Reply

  9. Awesome list. Such a good point about the money. Money is a tool, and can help you achieve some goals, but it won’t inherently make you happy or unhappy. Still, doing what you love and helping others while making a living doing that’s got to feel great.

    FWIW I’d rather be self employed. I like having the steadiness of a paycheck but would find more fulfillment from something else.

    Reply

  10. Congrats on two years of working for yourself! Once again you wrote something with an incredible amount of value. You spoke to a lot of the things I already struggle with or know that I will if I take the self-employment plunge.

    It’s definitely hard for most people to admit they suck at anything. But at the end of the day it’s probably better to try to improve further on your strengths instead of trying to improve a little on your weaknesses. If you’re not good at something, you’re just not good at it!

    I don’t know yet if being self-employed is the path I want to take. I think the main thing for me with that is the same as my quest for financial independence…just having options. The option of being able to quit my job to work for myself, if I want, would be nice!

    Keep up the great work!

    Reply

    • Thanks! Yes I agree that having the options is probably the most important part. Most people don’t want to be self-employed, and that’s OK! It’s not for everyone. There’s a ton of value in having a normal job and being great at it.

      Reply

  12. The two years of blogging is nice, but what you have achieved during these two years is really inspirational. I guess it took a lot of courage two years ago to step into the unknown, but if there’s no risk, then there’s no reward! Keep up the great work, not just in the next two years, but for much longer!

    Reply

  14. Love the insights and feel that every job comes with those “do it because its been done, or expected of you.” I’ve learned that missing out on those sometimes to live your life instead can reap huge benefits – work is part of our life, its not our life :).

    Thanks for the motivation to keep that in mind and in business to focus on what makes money.

    Have a great evening !

    Reply

  16. Congrats man! Dude I am so ready to be self-employed. I’m a federal employee and military reservist and I am DONE. I’ve just had enough. I’ve made the decision that my current job is the last time I will work for somebody else. I want to start a blog/site that teaches men how to have more confidence, shed bad habits, etc. I know they’re a dime a dozen these days but that just shows that there’s demand. I have something unique to offer so I’m gonna go for it! That course you’re setting up sounds like a great idea, I’ll keep it on my list of resources!

    Reply

  17. Great post. A lot of your lessons really resonated with me as I’m working on my blog as a side hustle. As I struggle to figure things out it’s good to hear that while you’ve been successful you still had to work at figuring everything out.

    Reply

  18. I thoroughly enjoyed this post. I’ve been following you for a while and finally decided that it was time for me to take the leap and begin my own blog. To answer your question, can I be self-employed and earn a steady paycheck? That would be the ideal situation!

    Reply

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